L-371,257: Difference between revisions
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{{Short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 444650848 |
| verifiedrevid = 444650848 |
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| IUPAC_name = 1-[4-[(1-Acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]-4-(2-oxo- |
| IUPAC_name = 1-[4-[(1-Acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]-4-(2-oxo-2''H''-3,1-benzoxazin-1(4''H'')-yl)piperidine |
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| image = L-371, |
| image = L-371,257.svg |
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| width = 225 |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B |
| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
| legal_status = |
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| routes_of_administration = |
| routes_of_administration = [[Oral administration|By mouth]] |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = |
| bioavailability = |
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| protein_bound = |
| protein_bound = |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = |
| excretion = |
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| CAS_number_Ref = {{cascite|correct|??}} |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 162042-44-6 |
| CAS_number = 162042-44-6 |
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| ATC_prefix = |
| ATC_prefix = None |
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| ATC_suffix = |
| ATC_suffix = |
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| ATC_supplemental = |
| ATC_supplemental = |
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| PubChem = 6918320 |
| PubChem = 6918320 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 5293524 |
| ChemSpiderID = 5293524 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| chemical_formula = |
| chemical_formula = |
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| C=28 | H=33 | N=3 | O=6 |
| C=28 | H=33 | N=3 | O=6 |
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| molecular_weight = 507.577 g/mol |
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| smiles = O=C1OCc3ccccc3N1C(CC4)CCN4C(=O)c2ccc(cc2OC)OC5CCN(C(C)=O)CC5 |
| smiles = O=C1OCc3ccccc3N1C(CC4)CCN4C(=O)c2ccc(cc2OC)OC5CCN(C(C)=O)CC5 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C28H33N3O6/c1-19(32)29-15-11-22(12-16-29)37-23-7-8-24(26(17-23)35-2)27(33)30-13-9-21(10-14-30)31-25-6-4-3-5-20(25)18-36-28(31)34/h3-8,17,21-22H,9-16,18H2,1-2H3 |
| StdInChI = 1S/C28H33N3O6/c1-19(32)29-15-11-22(12-16-29)37-23-7-8-24(26(17-23)35-2)27(33)30-13-9-21(10-14-30)31-25-6-4-3-5-20(25)18-36-28(31)34/h3-8,17,21-22H,9-16,18H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = WDERJSQJYIJOPD-UHFFFAOYSA-N |
| StdInChIKey = WDERJSQJYIJOPD-UHFFFAOYSA-N |
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}} |
}} |
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'''L-371,257''' is a compound used in scientific research which acts as a selective [[Antagonist (pharmacology)|antagonist]] of the [[oxytocin receptor]] with over 800x selectivity over the related [[vasopressin receptor]]s.<ref>{{cite journal | |
'''L-371,257''' is a compound used in scientific research which acts as a selective [[Antagonist (pharmacology)|antagonist]] of the [[oxytocin receptor]] with over 800x selectivity over the related [[vasopressin receptor]]s.<ref>{{cite journal | vauthors = Williams PD, Clineschmidt BV, Erb JM, Freidinger RM, Guidotti MT, Lis EV, Pawluczyk JM, Pettibone DJ, Reiss DR, Veber DF | display-authors = 6 | title = 1-(1-[4-[(N-acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]piperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist | journal = Journal of Medicinal Chemistry | volume = 38 | issue = 23 | pages = 4634–6 | date = November 1995 | pmid = 7473590 | doi = 10.1021/jm00023a002 }}</ref> It was one of the first non-peptide oxytocin antagonists developed,<ref>{{cite journal | vauthors = Bell IM, Erb JM, Freidinger RM, Gallicchio SN, Guare JP, Guidotti MT, Halpin RA, Hobbs DW, Homnick CF, Kuo MS, Lis EV, Mathre DJ, Michelson SR, Pawluczyk JM, Pettibone DJ, Reiss DR, Vickers S, Williams PD, Woyden CJ | display-authors = 6 | title = Development of orally active oxytocin antagonists: studies on 1-(1-[4-[1-(2-methyl-1-oxidopyridin-3-ylmethyl)piperidin-4-yloxy]-2- methoxybenzoyl]piperidin-4-yl)-1,4-dihydrobenz[d][1,3]oxazin-2-one (L-372,662) and related pyridines | journal = Journal of Medicinal Chemistry | volume = 41 | issue = 12 | pages = 2146–63 | date = June 1998 | pmid = 9622556 | doi = 10.1021/jm9800797 }}</ref><ref>{{cite journal | vauthors = Kuo MS, Bock MG, Freidinger RM, Guidotti MT, Lis EV, Pawluczyk JM, Perlow DS, Pettibone DJ, Quigley AG, Reiss DR, Williams PD, Woyden CJ | display-authors = 6 | title = Nonpeptide oxytocin antagonists: potent, orally bioavailable analogs of L-371,257 containing a 1-R-(pyridyl)ethyl ether terminus | journal = Bioorganic & Medicinal Chemistry Letters | volume = 8 | issue = 21 | pages = 3081–6 | date = November 1998 | pmid = 9873680 | doi = 10.1016/S0960-894X(98)00568-X }}</ref><ref>{{cite journal | vauthors = Williams PD, Bock MG, Evans BE, Freidinger RM, Gallicchio SN, Guidotti MT, Jacobson MA, Kuo MS, Levy MR, Lis EV, Michelson SR, Pawluczyk JM, Perlow DS, Pettibone DJ, Quigley AG, Reiss DR, Salvatore C, Stauffer KJ, Woyden CJ | display-authors = 6 | title = Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency | journal = Bioorganic & Medicinal Chemistry Letters | volume = 9 | issue = 9 | pages = 1311–6 | date = May 1999 | pmid = 10340620 | doi = 10.1016/S0960-894X(99)00181-X }}</ref><ref>{{cite journal | vauthors = Wyatt PG, Allen MJ, Chilcott J, Foster A, Livermore DG, Mordaunt JE, Scicinski J, Woollard PM | display-authors = 6 | title = Identification of potent and selective oxytocin antagonists. Part 1: indole and benzofuran derivatives | journal = Bioorganic & Medicinal Chemistry Letters | volume = 12 | issue = 10 | pages = 1399–404 | date = May 2002 | pmid = 11992786 | doi = 10.1016/S0960-894X(02)00159-2 }}</ref> and has good oral bioavailability, but poor penetration of the [[blood–brain barrier]], which gives it good peripheral selectivity with few central side effects.<ref>{{cite journal | vauthors = Ring RH, Malberg JE, Potestio L, Ping J, Boikess S, Luo B, Schechter LE, Rizzo S, Rahman Z, Rosenzweig-Lipson S | display-authors = 6 | title = Anxiolytic-like activity of oxytocin in male mice: behavioral and autonomic evidence, therapeutic implications | journal = Psychopharmacology | volume = 185 | issue = 2 | pages = 218–25 | date = April 2006 | pmid = 16418825 | doi = 10.1007/s00213-005-0293-z | s2cid = 13647805 }}</ref> Potential applications are likely to be in the treatment of premature labour.<ref>{{cite journal | vauthors = Hawtin SR, Ha SN, Pettibone DJ, Wheatley M | title = A Gly/Ala switch contributes to high affinity binding of benzoxazinone-based non-peptide oxytocin receptor antagonists | journal = FEBS Letters | volume = 579 | issue = 2 | pages = 349–56 | date = January 2005 | pmid = 15642343 | doi = 10.1016/j.febslet.2004.10.108 | s2cid = 38088139 | doi-access = free }}</ref> |
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==See also== |
== See also == |
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* [[Atosiban]] |
* [[Atosiban]] |
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* [[Barusiban]] |
* [[Barusiban]] |
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* [[Retosiban]] |
* [[Retosiban]] |
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==References== |
== References == |
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{{Reflist|2}} |
{{Reflist|2}} |
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{{Oxytocin and vasopressin receptor modulators}} |
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{{Neuropeptidergics}} |
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[[Category:Tocolytics]] |
[[Category:Tocolytics]] |
Latest revision as of 23:47, 12 August 2023
Clinical data | |
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Routes of administration | By mouth |
ATC code |
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Chemical and physical data | |
Formula | C28H33N3O6 |
Molar mass | 507.587 g·mol−1 |
3D model (JSmol) | |
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(what is this?) (verify) |
L-371,257 is a compound used in scientific research which acts as a selective antagonist of the oxytocin receptor with over 800x selectivity over the related vasopressin receptors.[1] It was one of the first non-peptide oxytocin antagonists developed,[2][3][4][5] and has good oral bioavailability, but poor penetration of the blood–brain barrier, which gives it good peripheral selectivity with few central side effects.[6] Potential applications are likely to be in the treatment of premature labour.[7]
See also
[edit]References
[edit]- ^ Williams PD, Clineschmidt BV, Erb JM, Freidinger RM, Guidotti MT, Lis EV, et al. (November 1995). "1-(1-[4-[(N-acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]piperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist". Journal of Medicinal Chemistry. 38 (23): 4634–6. doi:10.1021/jm00023a002. PMID 7473590.
- ^ Bell IM, Erb JM, Freidinger RM, Gallicchio SN, Guare JP, Guidotti MT, et al. (June 1998). "Development of orally active oxytocin antagonists: studies on 1-(1-[4-[1-(2-methyl-1-oxidopyridin-3-ylmethyl)piperidin-4-yloxy]-2- methoxybenzoyl]piperidin-4-yl)-1,4-dihydrobenz[d][1,3]oxazin-2-one (L-372,662) and related pyridines". Journal of Medicinal Chemistry. 41 (12): 2146–63. doi:10.1021/jm9800797. PMID 9622556.
- ^ Kuo MS, Bock MG, Freidinger RM, Guidotti MT, Lis EV, Pawluczyk JM, et al. (November 1998). "Nonpeptide oxytocin antagonists: potent, orally bioavailable analogs of L-371,257 containing a 1-R-(pyridyl)ethyl ether terminus". Bioorganic & Medicinal Chemistry Letters. 8 (21): 3081–6. doi:10.1016/S0960-894X(98)00568-X. PMID 9873680.
- ^ Williams PD, Bock MG, Evans BE, Freidinger RM, Gallicchio SN, Guidotti MT, et al. (May 1999). "Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency". Bioorganic & Medicinal Chemistry Letters. 9 (9): 1311–6. doi:10.1016/S0960-894X(99)00181-X. PMID 10340620.
- ^ Wyatt PG, Allen MJ, Chilcott J, Foster A, Livermore DG, Mordaunt JE, et al. (May 2002). "Identification of potent and selective oxytocin antagonists. Part 1: indole and benzofuran derivatives". Bioorganic & Medicinal Chemistry Letters. 12 (10): 1399–404. doi:10.1016/S0960-894X(02)00159-2. PMID 11992786.
- ^ Ring RH, Malberg JE, Potestio L, Ping J, Boikess S, Luo B, et al. (April 2006). "Anxiolytic-like activity of oxytocin in male mice: behavioral and autonomic evidence, therapeutic implications". Psychopharmacology. 185 (2): 218–25. doi:10.1007/s00213-005-0293-z. PMID 16418825. S2CID 13647805.
- ^ Hawtin SR, Ha SN, Pettibone DJ, Wheatley M (January 2005). "A Gly/Ala switch contributes to high affinity binding of benzoxazinone-based non-peptide oxytocin receptor antagonists". FEBS Letters. 579 (2): 349–56. doi:10.1016/j.febslet.2004.10.108. PMID 15642343. S2CID 38088139.